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In this episode of The Strategy Layer Live, Steve sits down with Richard Bird—multi-time CISO, former Chief Customer Information Officer at Ping Identity, author, and current Chief Security Officer at Singulr—for a conversation that pushes beyond conventional cybersecurity narratives.

For the first time on the podcast, an AI digital twin takes an active speaking role, opening the episode with a blunt assessment of where cybersecurity thinking has already fallen behind. From there, the discussion moves into the strategic implications of AI across cybercrime, governance, leadership, and careers.

This episode explores how AI is reshaping the threat landscape faster than most organizations are prepared for, why governance failures are increasingly systemic rather than technical, and what leadership looks like when machines operate at scale and speed. The conversation also turns personal, with reflections on Richard’s book Famous With 12 People and the legacy he hopes to leave behind.

Key Topics Discussed

• AI Digital Twins in Leadership Conversations
  What it means when AI systems don’t just assist—but actively participate in strategic dialogue.
• AI and the Acceleration of Cybercrime
  How attackers are using AI as force multiplication while many organizations reduce human defenders.
• Shadow AI and Unfinished Security Work
  Why decades of unfinished IT and security projects created the conditions for today’s AI risk.
• Governance Failures Are Systemic, Not Technical
  How leadership blind spots—not tooling—are driving AI governance gaps.
• Identity, Access, and Ownership in an AI World
  Why diffuse responsibility leads to no accountability when AI systems act at scale.
• The Future of Consulting and Verified Intelligence
  How AI is reshaping advisory work and exposing performative expertise.
• Career Strategy and Influence
  Insights from Famous With 12 People on building impact through depth, clarity, and relevance.
• Legacy and Leadership
  Richard’s reflections on service, contribution, and what comes next beyond titles and roles.

Insightful Takeaways

• AI rewards preparedness, not optimism.
  Attackers are using AI to move faster and more efficiently; organizations that fail to adapt governance and defenses will see the results in loss curves.
• Shadow AI is a leadership problem before it’s a technology problem.
  Uncontrolled AI use is the predictable outcome of years of tolerated sprawl and unfinished security work.
• Cutting people while attackers scale with AI is a dangerous asymmetry.
  AI augments those who use it strategically—and penalizes those who remove human judgment from critical systems.
• Governance must evolve from policy to ownership.
  When everyone owns identity, risk, or AI outcomes, accountability disappears.
• Impact comes from depth, not scale.
  Leadership, influence, and career growth are built by being meaningful to a few—not visible to everyone.
• Legacy is defined by service, not status.
  The most durable contribution comes from helping others move forward—especially in moments of uncertainty and change.

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In this episode of The Strategy Layer Live, Steve sits down with Bill Kehoe, Chief Information Officer for Washington State, for a rare, wide-ranging conversation recorded in person. Bill reflects on a career spanning state, county, and local government — and the leadership lessons he learned along the way.

From transforming the DMV experience in the early 2000s, to championing digital equity and modernizing resident identity services, to leading with calm resolve in the face of cybersecurity threats, Bill shares what it means to serve with purpose in the digital age.

What We Cover in This Episode

• Bill’s early path into public service and what has kept him committed for decades
• The turning-point projects that shaped his leadership philosophy
• Lessons from running and coaching — discipline, strategy, and individual development
• The bold vision behind digital equity and the Resident Portal
• Modernization without fear: incremental change, customer experience, and agile delivery
• The Resident Portal Challenge and the future of procurement innovation
• Multi-vendor collaboration and why competition can create better outcomes
• The CIO–CISO partnership and shared responsibility for cybersecurity
• Leading through complexity with calm, clarity, and trust
• Bill’s reflections on legacy, public service, and the next generation of leaders
• How AI is reshaping responsibility, decision-making, and efficiency in government

Quote of the Show:

• “I’m the front lines for everything that happens — good or bad — and I consider myself accountable and responsible for everything that goes on in my agency and in technology in the state.” - Bill Kehoe

Links:

• https://watech.wa.gov/
• https://www.linkedin.com/in/william-kehoe-a37a0714b/

#PublicSectorLeadership #GovernmentTechnology #CybersecurityLeadership

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In this episode of The Strategy Layer Live, we sit down with one of the most respected and candid voices in cybersecurity today — Jimmy Sanders.

Jimmy is the CISO of Save Mart overseeing more than 200 stores across the West Coast, the former CISO of Netflix DVD, and the current President of ISSA International — giving him a rare, global vantage point on how the role of CISO is being redefined in real time.

But this conversation isn’t just about job titles. It’s about transformation.

Together, Steve and Jimmy dive into how the CISO role is shifting from technician to strategist, why governance frameworks often crumble under real-world politics, and what it takes to lead when budgets are flat, expectations are exponential, and trust is the only currency that matters.

What we cover in this episode:

• Why automation must come before AI — and how to prepare your team for agents
• The hidden costs of being “just the technician” instead of the strategic partner
• The politics of governance and why frameworks often fail without enforcement
• How to measure human-centered risk: burnout, fatigue, and decision friction
• Why trust and presence — not titles — determine whether you get heard at the board level
• The future of the CISO: from risk manager to Chief Trust Officer, or even CIO

Whether you’re leading your first security team or steering global strategy, this episode will challenge you to rethink what leadership looks like when the CISO’s true mandate is to create resilience, not just reduce risk.

Visit www.strategylayer.com for more episodes like this.